Quick take:

• Yes, the sample I looked at did have some very expensive retreats, and I think you can run much cheaper ones. Note though that EAGx events / conferences can also be much cheaper so you should adjust on both sides (I think I had a cost-inflated sample due to high spending on community building in 2022)
• I still think outcomes-per-person at retreats often don't seem that different to larger events, so returns to scale are often real. i.e. focus on cost-per-attendee. If your theory of change involves helping lots of people you don't know well find careers in EA/AIS, I think going bigger is usually a good move.
• Retreats are definitely a useful intervention, especially when you have a smaller group whose needs/goals you know well (e.g. more involved community members looking to go deeper on topics).

I had a reminder to check back on this. I had a quick scan, and I don't think this happened. Joe's post probably meets the bar, and does suggest it's still a contentious issue, but I can't find 9+ more so not as contentious as you predicted :)

Awesome line-up, nice work!

Starting afresh seems like the right move here, and I think it's super commendable to share that you're re-committing. 

I have the same problem when it comes to end of year donations, and that prompted me to move to monthly donations (even if the idealized version of me would save accordingly and then make bigger donations more thoughtfully EOY).

Also:

In total, I’ve given about half of what I pledged since 2016.

This is still a lot of money, and a lot of good. Giving 5% of your income to charity for almost 10 years is a hugely generous and selfless thing to do :)

Cool! FYI when I open your home page on a large monitor, the "Log In" and "Blog" buttons overlap with each other (fine on small screens).

You might still want more on the margin, but I think this already happens a fair amount in EA:

• Fellowships are very common—the amount of freedom seems to vary but many (e.g., GovAI, historically FHI) involve giving fellows several months or up to a year to explore topics with limited oversight.
• EA funders often give unrestricted funding, often to individuals to pursue projects (see e.g. EA Funds grants, ACX grants, Manifund).
• Compared to other social/intellectual movements, EA is (still) well-funded. I expect many other non-profits / activist groups / academic institutions would be amazed at how many people in EA are paid well to think and write about relevant topics with a lot of freedom.

+1. Bumping my quick take listing where some of the people who participated in my EA uni group while I was there ended up (this is now considerably out of date, but AFAIK these people remain on paths that seem super impactful)

It looks the post in question is now tagged 'Community'.